


The Business of Sex

by Luces



Category: World Wrestling Entertainment
Genre: Anal Sex, Bars and Pubs, Escort Service, F/M, Oral Sex, Prostitution, Spanking, Vaginal Sex, episodic series, first orgasms
Language: English
Status: In-Progress
Published: 2014-02-24
Updated: 2014-05-17
Packaged: 2018-01-13 14:06:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 12,867
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1229266
Author URL: https://archiveofourown.org/users/Luces/pseuds/Luces
Summary: <blockquote class="userstuff">
              <p>AU episodic series. They call me Big Mama. I run a male escort service, but we all know what the customers really want. I have a fine collection of men, but the one they call Ambrose, the one who would be my crown jewel, has continued to elude me until tonight.</p>
            </blockquote>





	1. A Business Proposition

They call me Big Mama. Of course, that’s not my real name, but that information is only disclosed to a few people. I am a woman of high tastes, which have been afforded to me by my wealthy husband’s untimely death. Don’t get the wrong idea, he died of natural causes. I married at 22 to a business man in his 60s. I can’t say I was particularly attracted to him, but I was young, foolish, and in a lot of debt from college, so I accepted his attempts to woo me. Nine years later, he passed away and had left everything of his in my name. It was a very comfortable life, but I soon grew bored. I needed a hobby.

I collect boys. Well, that makes it sound like I keep them in glass cases in alphabetical order. I collect boys in the sense that I employ them for my business and my own personal enjoyment. I’m a madam for young male prostitutes. I pay them a monthly salary and they live with me for free in the small mansion my husband left. Like I said, he was quite wealthy. We work under the title of an escort service, but let’s be frank. When a man or a woman comes to me, they are looking to get fucked and fucked well. We have a very good reputation in the seedy world of prostitution. I pride myself in presenting the best that the city has to offer. My collection is a fine example of the male specimen, but one has continued to elude me.

His name is whispered in hushed tones across dark alleyways. I hear customers gossiping rumors about him. He goes by many names: Mox, Street Dog, Ambrose. I don’t know which he likes to use officially, but by using so many different names, it has been hard for me to track him and get my hands on this prized man. After months of searching, I finally found him and now he was within my crosshairs.

I had been watching him across the smoke filled room for about an hour. He nursed a glass of whiskey, simply observing his surroundings. He was looking quite dapper in a clean cut suit with his hair slicked back. I saw him pull out a cigarette and he patted down his jacket looking for a lighter. Time for me to make my move.

I walked over to him and lit up a lighter in front of his face. He looked up at me with those electric eyes, paused, and then leaned in to catch his smoke on the flame.

"You know, not many people these days have the common courtesy to offer a man a light," he said as he exhaled that first drag.

"I pride myself in old fashioned values. Mind if I sit down?"

He gestured to a seat and leaned back in his own.

"They call me..."

"I know who you are," he interrupted. "And it's clear that you know who I am. What do you want from me?”

"I have a business proposition for you," I explained. "I have a fine collection of boys at my disposal, but I'm looking for the best. You've eluded me for a long time, street dog."

He narrowed his eyes at me, his face contorted into a grimace.

"Don't call me that." He took another drag. "I hate that that's one of the names lurking around out there."

“Then what would you like me to call you? You do go by many names.”

“For you," he paused, eyeing the room to make sure no one was paying attention. He leaned close to my ear, his lips gently brushing against my ear. "You can call me Jon, gorgeous."

"Unnecessary flattery upsets me, Jon,” I said quietly.

"That wasn't flattery, Mama, and it was definitely necessary." His eyes burned with passion and desire and I couldn't tell if it was genuine or part of the job. Oh, he was good.

I cleared my throat, trying to not let his words and his calm, raspy voice get to me. There was enough time for that later. Business first.

"I have to say I like how clean and professional you look. Many of my boys were very scrappy when I took them in. You've clearly been at this a while and have a great reputation."

“Well I normally don't dress like this, but my customer earlier tonight wanted the 007 package, so that's what she got."

"And what makes up that? Russian spies and espionage?"

"I drive her around in a nice car I rent. Then we drink martinis, shaken, not stirred, of course. And then I fuck her brains out." He took a slow long drag and leaned his head back, his face reflecting pure ecstasy. He held his breath for a moment, keeping the nicotine laced smoke in his lungs. I couldn't help but stare at him. He wasn't particularly beautiful, but there was something about him that made you want to stare and never let him out of your sight. I knew I wanted him for my collection; that was a definite. He would be my crown jewel. I just had to see if we would be a good fit for a business partnership. He exhaled the smoke just as slowly as he had inhaled it. He brought his head back upright and opened his eyes, staring directly into mine. They seemed to constantly change color in the clouded light of the bar. He was definitely trying to seduce me like I was a customer, and I had to keep my guard to make sure I didn't fall into trap. If I was to be seduced, it was going to be on my own terms. "That last part is standard procedure with all of my services." His mouth drew into an arrogant smirk. I had to admire his confidence.

"Good to know. I expect my boys to always deliver."

"Don't worry. I always deliver. Usually multiple times." He took a sip of his whiskey and placed the glass back down gently. He then wiped his mouth by dragging his index finger across his lips. I flinched slightly at the sight. I knew I had to refocus as he was beginning to win and he knew it. He's just another potential employee, a commodity. I am the boss here, not him.

"So if I decided to work with you instead if continuing on my own, what would be in it for me?" he asked.

"I accommodate all of my boys with generously sized rooms in my mansion. They get a monthly salary that we agree to in advance and renegotiate annually. I deal with marketing them so that together we can make the most money possible. I also supply them with the best health care available and require constant testing for STDs. In return, I can use then at my disposal. I don't mean that in a disrespectful way. I love and care for all of my boys, but if I get lonely, I'll come to whomever I please and whatever Mama wants, she gets. I also have an open door policy. If any of the boys no longer want to work for me, we discuss their issues and they then either decide to stay or leave. Like I said, I do have a reputation to maintain. But most of my boys seem to enjoy working for me. Which leads me to you. I want you. You would be my highest paid boy and if the rumors are true, you would demand the highest price for your work. Just by looking at you right now, I imagine it would be quite worth the money."

He inhaled his cigarette and exhaled some smoke rings. I could only imagine the other things that clearly talented mouth could do. "That all sounds pretty agreeable." He ran his free hand through his hair, loosening strands from their slicked state so that some fell in front of his eyes. "Rumors, huh? So where do we go from here?" he asked.

"Well, normally we retire back to my place for the, shall we say, practical part of the interview." I let my eyes drink in his full frame as he stood from his chair.

"My place is closer." He reached his hand out and helped me out of my seat. What a gentleman. I left money on the table to cover his drink and an extravagant tip.

We exited the bar and he pointed down in the direction we were to head. We walked in silence for a while until I eventually broke the silence. It was time to begin the test drive. "I'd like you to give me a look into the variety of services you will offer my customers. It allows me to see what you've got up close and personal and helps me get an idea of how to market you. Not that I think it would-"

Before I could finish my sentence, he grabbed my arm and pulled me into a dark alley. He pushed me back hard against a wall and pinned my shoulders down with his hands. His mouth began to attack my neck, kisses speckled with bites trailing down to my collarbone. He roughly shoved his hand under my dress, pushed my panties to the side, and slid two fingers up inside of me. It was a good thing that I was already very aroused from his flirtations earlier or his roughness would have hurt. He thrust his fingers slowly, focusing more on how hard and deeply he was working them. I lifted one of my legs and wrapped it around his hip, allowing him more access. He pulled at the neckline of my dress and rested his head next to mine so that we could hear each other's heavy breathes.

Just as I was about to orgasm around his fingers, he pulled them out and brought then up to my mouth. I opened my mouth, granting then access, and sucked off my fluids. He then took my hand and guided me back to the main road as we continued to his apartment.

His change in demeanor was instantaneous and almost disturbing in how seamlessly he was about to go from a rough street animal to a perfect gentleman. He took his jacket off and draped it over my shoulders. I thanked him and he slipped an arm behind my back, cradling my hip in his hand. It felt very romantic. I imagine many young ladies would love their first time to be like this, the way he is right now.

We arrived in front of a shabby looking building and he led me up the stairs. He opened the door and gestured inside. "Ladies first," he said as he bowed slightly.

The building looked just as run down on the inside as it had on the outside. "With how much money you must be making, I would have imagined you living in a much nicer place," I said as I started up the stairs.

He broke character for a moment to answer my inquiry. "Whatever I have leftover from the hotel fees and clothing and car rentals, I save. I didn't come from much growing up, so I know how to save. I know I can't do this forever, so I want to protect my future."

"I want to protect you and your future too, Jon. I really do hope you come to live with me."

He stopped in front of a door and opened it. "It would be a shame for a lady such as you to have to protect a man like me. Now come inside so I can spoil you." And with that, he was back into character.

His apartment was surprisingly clean. I was especially pleased at how clean his bed was. I would enjoy making it dirty with him.

I kicked off my heels and started to take my nylons off when he grabbed my hand to stop me. "Baby, that's my job." He crouched down in front of me and slid his hands up my legs from my ankles to my hips. He grasped the top of the nylons and slowly peeled them down, looking up at me watching him the entire time. I stepped out of the thin fabric when it hit the floor. As he stood up again, he held the balled up nylons up to his nose and inhaled. “I love that this smells like you.” I couldn’t help but blush. He circled behind me and placed his hands on my shoulders, gently rubbing them. His fingers then traced their way down to the zipper of my dress. He kissed my shoulder and the side of my neck as he pulled down on the zipper slowly so that I could hear the sound of each tooth coming apart. Bring his hands back up to my shoulders, he slid the straps to the side and the entire dress fell to the floor. “Turn around and let me see you,” he said. I looked over my bare shoulder at him before the rest of my body followed. He looked me over, then cupped my face and sighed. “You are so beautiful.” Oh yes, this was going to be a popular choice.

I turned around and sat on the edge of the bed, leaning back and crossing my legs. “So, do I get to watch you undress for me now?” He slowly raised his head and his gaze me mine for a moment before he looked away. He wrapped his arms around his chest and slinked back slightly.

“I…I’m nervous,” he said in a voice to soft and quiet that I almost didn’t hear it.

“Aww, are you shy, sweetheart? It’s okay. Is this your first time getting naked in front of anyone?” He paused and then nodded quickly. I stood up and slowly walked over to him. “Let me help you with that.” I rubbed my hands on his chest and slowly unbuttoned his shirt, leaning in to gently kiss his lips. They were soft and warm and I melted into the kiss. I have to admit that I was partial to a first time fantasy. There’s just something about corrupting an innocent. Together we slipped his shirt off and then I moved on to the best part. I traced my fingers down and undid his pants, tugging on the lightly and letting gravity do the rest.

I cupped his erection with my hand through the thin fabric of his boxer briefs and brought my mouth to his ear. “Let me show you how to use this, honey.” I knelt down onto my knees and brought my mouth to his groin, brushing my lips up and down his covered cock. My fingers slipped underneath the hem and slowly removed his underwear. His erection fell out and I caught the tip in my mouth, slowly sucking in the entire length.

He let out a soft moan and placed his hand on the back of my head. “Your mouth feels so good on me, mistress.” I had to laugh at his choice of words. His grip on my head tightened and he pulled my head back. “No one fucking laughs at me, bitch,” he said through dark eyes that sent bolts of fear and excitement through my body. He held my head still and began to quickly thrust in and out of my mouth. Tears started to well in the corners of my eyes as he went. He was pushing his entire length down my throat and it had been a while since I had not been in control of a blowjob. I relaxed my body and just enjoyed being dominated like this. I am the boss when it comes to my business, but I will gladly let one of my boys be the boss of me behind closed doors.

His own moans grew louder than mine and I could feel his cock tighten between my lips. He suddenly slipped out and pushed my face with his hand so hard that I fell onto my back. I looked up at him standing over me, my face drenched in lust as I studied his naked form. I have to be the luckiest woman in the world right now.

“Get on that bed, slut.” I eagerly complied, lying down on my back with my upper body propped up by my elbows. I watched him as he slowly swaggered towards me, rubbing his hands together and sticking his tongue out. I could feel myself getting wetter wondering what was going through that magnificently twisted mind of his. He climbed onto the bed with me and slowly crawled forward. He teasingly pulled of my panties and flung them to the side. He bent down again so that his head was positioned between my legs. “This right here is one of my specialties.” I watched in awe as he lowered his mouth and began to lick my pussy. I’m not quite sure exactly what he was doing down there with that tongue of his because my logical brain immediately shut off and primal id took over. I clawed and scratched at the bed sheets and my hips began to thrash about. He clearly knew how I was going to react and how to respond because he gripped tightly on my hips and held them down firmly so he could continue working. I felt that orgasmic fire that I loved so dearly burning between my legs and I quickly came, my hands grabbing onto his hair and holding his head down as I did.

When I finally let go and allowed him to come up for air, I laid there for a moment composing myself. “Jesus Christ, Jon. You could become a very wealthy man with that mouth,” I gasped. He wiped his mouth off with the back of his hand and smiled at me. I noticed that he had cute little dimples when he did. Good lord, no wonder he has been leaving a trail of satisfied men and women in his wake. If by the end of this evening, he didn’t decide to work with me, it would still have been worth it after this. Wait, did I say with? I’ve always said work for in the past. Damn him. His sexual prowess was making me soft.

He, however, was still quite hard. He hopped off of the bed to grab a condom, rolled it on, and returned. He lay down next to me and gently traced his fingers along the lines of my body. “Do you know just how beautiful you are?” he asked. I laughed quietly at his question, but couldn’t stop myself from falling under that spell of his. He positioned himself on top of me and sweetly kissed my lips. He ran his fingers through my hair as he kissed me and with his free hand, lined up his erection and gently pushed inside of me. He thrust slowly, focusing on the intimacy of the moment rather than the carnal pleasure of it. Even though I knew that he was simply presenting me with one of the services he provides, I wanted to believe that this tenderness than he was showing me was real. It was very difficult to not fall for him.

I came again while he was making love to me. It wasn’t nearly as intense as the first one, but it flowed through my whole body and made me smile. I sighed and stroked his head. I really did want to protect his future and keep him safe and happy.

He pulled away from me and dragged his nails across my stomach. He scooted back and flipped me over, pulling up my hips so that I was on all fours. He slipped a thumb into my wet pussy and then pulled it out again. I gasped when he pressed that same thumb against my asshole. Spreading my fluids around the entrance, he slowly penetrated that barrier and allowed my body to relax around his thumb. He thrust in and out a few times, twisting his hand while he did, before he pulled it out again.

“There’s some lube in the nightstand drawer, honey,” I whispered, eager to experience his grand finale. He reached over and pulled out the bottle and covered his cock with the slick liquid. He rubbed the head onto my hold and carefully began to push inside. I closed my eyes and let out a long quiet moan as he stretched and filled me. He paused while my body adjusted to this breach of privacy. I lifted my head and nodded to let him know that I was ready for him to give me everything he had.

He started out thrusting slowly at first, gradually gaining momentum. My moans were loud and frequent as he fucked my ass. His hands dug hard into the flesh of my hips. I threw my head back and begged for him to go harder. He reached a strong hand forward and wrapped it around my neck, pulling me back slightly and making my breaths a little more labored. I felt lightheaded as he continued to thrust away and it didn’t make matter better when he wrapped his other hand around my waste and rubbed my clit with his finger. It was all too much for me and came quite hard, my body gripping around his cock as I did. That must have been too much for him as well because he squeezed my throat harder and let out a loud curse as he pulsed inside of me.

He let go and my body collapsed on the bed. I could barely speak, let alone move. He got up to dispose of the condom and came back with a lit cigarette between his lips. He sat down in a chair a few feet from me, slowly inhaling and exhaling a cloud of smoke. “So what do you think?” he muttered in my direction.

It took me a moment to respond to him. “Do I have to put it into words? I’m a puddle of a woman over here. You’re so damn good that I can’t tell if any of that was real or just you working.”

He took a slow drag on his cigarette and shrugged his shoulders, smirking as he exhaled the smoke through his nose.

“How about you? Have you decided if you’ll come to work with me? If it isn’t already obvious, I would love to have you.” I paused for a moment and then quietly mumbled, “You’re already my new favorite.”

“Yeah, I will,” he replied. “I already knew I was going to before you offered me a light earlier. You say you’ve been looking for me for a while, but I’ve been watching you, too. I was just waiting for you to come to me, Mama. I gotta have the upper hand somehow.”

“Well you were certainly not lying before. You definitely did deliver…multiple times.”

He smiled that cheeky grin from before as he stood up and sauntered back over to me. I rolled onto my side and sat up on the edge of the bed. I reached out my hand to shake his and he took it in his own. I had to contain my giddiness at our agreement.

“I’ll be in touch to make arrangements for you to move in this week,” I said as I began to gather my clothes to get dressed.

He grabbed my wrist and pulled me against him. “You can get dressed in the morning.”

So ladies, gentleman, if you’re ever feeling a little lonely and would like some company, come and visit Big Mama’s and we’ll treat you right.  We have a fine selection of men to choose from, but if you have the money, give a chance to our newest escort. He is worth every penny, and you can trust me on that.


	2. Ambrose and the "Frigid" Woman

**Summary for the Chapter:**

> A young woman named Rachel can't seem to orgasm, so she hires Ambrose to try to help her.

**Chapter 2**

                "I love all my boys, but you are definitely my favorite,” I groaned as I stretched out in bed.

It had been about two months since Jon came to live with me at the mansion. He had already brought in more income than I could have ever dreamed. I barely had to do any real advertising for him. Clearly the Ambrose name, which he chose to continue to use, carried a lot of weight.

"There's just something about you, darlin. You seem to be able to understand exactly what someone needs and how to give it to them." I rolled to the side and propped my head up on my arm. He lit up a cigarette and sunk back down into the bed.

"It's a blessing and a curse, really," he sighed as he exhaled. I laughed at his shameless cockiness. I would've been irritated by it if he wasn't as professional as he was and if he wasn't so damn good at his job.

"Well, that was a very enjoyable break, but I need to get back downstairs and start working on this week's budget. Thank you very much, Mr. Ambrose." I leaned down and gave him a kiss on the cheek.

"Anything for you, Mama."

* * *

 

As I came down the stairs into the large foyer that doubled as the lobby for the brothel, I noticed a petite young woman staring at the pictures of my boys on the wall. I could tell from her body language that she was very nervous. When I reached the bottom of the stairs, I stopped and watched her for a moment. She spent a good while in front of each boy's photo, but when she got to Jon's, I noticed her linger there a little longer and I could hear her sigh rather loudly.

"He's a handsome son of a bitch, isn't he?" I asked suddenly, making her jump.

"Oh. Um...yes. He is, uh, ma'am," she answered. Her voice was quiet and weak. Now I was wondering if she had somehow wandered in here by accident.

"Honey, I hate it when people call me ma'am. Please, call me Big Mama." I held out my hand as I approached her. She tentatively gave me hers. Her handshake left much to be desired. "Is there something I can do for you today, sugar?"

"I don't really know. Am I allowed to say that I'm just looking?"

I laughed at her honesty. "I suppose you could, honey, but I've never had anyone come in here just to browse. Everyone has a specific reason for showing up, whether they have a particular fantasy they want to explore or they're just lonely. You must have a reason for stepping over the threshold of that door."

                She lowered her head and twiddled her thumbs. It looked like something was right on the tip of her tongue when a door to the left swung open and a handful of the boys came up from the gym. I couldn’t help but sneak a peek at their sweat drenched bodies. That particular sight always got my heart racing. I shook off my excitement and turned back to the young customer. Her face was as red as a ripe tomato and she was standing in a different position than before. I assumed that seeing the boys had made her nervous.

                “Are you okay, honey? Why don’t we go into my office where we can talk privately without all those pesky boys interrupting us.” I smiled warmly at her and beckoned for her to follow me.

                “Now tell me what your name is, sweetheart,” I said as I shut the door behind me.

                “Rachel, ma’am. I’m sorry, I mean Big Mama.”

                Despite the slip of her tongue, I liked this young lady. I found her innocence quite refreshing, especially in my line of work.

                “I’m going to cut to the chase, Miss Rachel. Are you a virgin?”

                To my surprise, she laughed.

                “Not in the least! I’m 24 now and I lost my virginity when I was 17. So definitely not a virgin, Mama. “

                “I can’t say I’m not surprised. You seemed so timid and uncomfortable out there in the lobby, especially when the boys came through. I just thought that may have been the case.”

                “I’m just nervous to be in a place like this. That’s all. I’m a virgin when it comes to the sex industry,” she explained, a small smile on her lips.

                “Well, we all have to start somewhere, honey. So now that we’re in private, why did you decide to come here today and what can I do to help you fulfill that need or desire?”

                “Umm…well…the truth is…” She continued her sentence, but her voice became so quiet and mumbled that I couldn’t make out what she was saying.

                “I’m sorry, honey, you’re going to have to speak up,” I pleaded.

                “The truth is, I’ve never had an orgasm. I’m able to become aroused enough, I think, but I’ve never been able to orgasm for some reason. I’ve had plenty of sex, especially in this past year. I’ve been slutting it up, trying all sorts of different partners, searching for what is apparently my white whale. Coming in here today is my last ditch attempt before I visit a doctor to see if something is physically or mentally wrong with me.” She let out a long sigh, like she had been holding all of that in for a while and it felt good to finally get it out.

                “Is that all? Oh honey, don’t you worry, I have the perfect gentleman to help you out with that pesky problem.”

* * *

 

                About a week later, it was time for Miss Rachel to finally capture that elusive orgasm. Or at least give a fair fight for it. That morning I had given the boys their daily schedules as usual, but I told Jon to hang back for a moment.

                “What’s up?” he asked.

                “So I blocked you off for the entire day. I have a special assignment for you, my love.”

                “Oooh, a special assignment, huh? Like a challenge? You know I love testing out my…abilities.”

                “Oh yes, love, this will definitely be a test of your abilities,” I replied. “Your customer for today is Miss Rachel. This lovely young lady has never had an orgasm before.”

                “I call bull shit.”

                “I’m fairly certain that it’s legitimate. If she had been lying, she wouldn’t have been so physically distraught when she came in last week. Her body language told me she was genuine.”

                “Huh. Poor thing, then.”

                “Don’t you dare go feeling sorry for her. I doubt she’s going to feel comfortable and sexy with you pitying her, honey. She said that she’s been with many partners, but still no orgasm. She’s on the verge of going to see if there’s a medical or psychological reason behind it if you and her aren’t able to get her to come tonight. I booked her for the whole day because I’d like you to spend time with her and get to know her. It seems like she’s a timid girl overall, so if you were to just go in for the kill, I think she would be very intimidated. She should be relaxed and confident when it’s time for you to do your thing. I gave her my word that you would do everything you could to help her out with this…” I placed my hand on his cheek. “…so don’t fuck it up. Now go get ready. I told her to be here at 10am to meet you.” I walked around him and smacked his jean-clad ass as I went by. It’s good to be the boss sometimes.

* * *

 

                Not entirely knowing what to expect from this woman, he chose to wear a pair of nice black slacks and a crisp blue button up dress shirt. He figured it would be a safe bet to go with the clean well-dressed look rather than his preferred slacker look. If this chick turned out to be cool, he could always change later, but most of his customers tended to enjoy a more formal look from him.

                He went outside to smoke while he waited for her to arrive. When she pulled up and got out of her car, he approached her and held out his hand.

                “You must be Rachel,” he mumbled over his cigarette before he spit it on the ground and stubbed it out. She stood frozen, staring at his hand. “You okay?” he asked.

                She shook her head and accepted his hand.  “I’m sorry…it’s just that she didn’t tell me it was going to be you.”

                “Oh? Is that a bad thing?” he laughed.

                Her face clearly reflected the embarrassment that she felt. “No, it’s not a bad thing. I’ve just…um…I’ve seen your picture on the posters and I’ve used it to…you know…fantasize…” She was barely audible on the last work, but he knew what she had said and he wasn’t about to make her repeat it.

                “Why don’t you come take a walk with me, Rachel, and let me get to know you a little bit. I like to talk with my customers ahead of time so I can get a feel for them.”

                They had been walking in silence for a few minutes, enjoying the fresh morning air. Rachel had her head down, still feeling nervous standing next to this man whom she had tried to pleasure herself to once or twice. He could tell that she was uncomfortable, so he motioned to a nearby tree and they went to sit down.

                “So tell me about yourself. I want to know how I can get you off.” He took out another cigarette and offered her one, but she turned it down.

                “I’m 24 and until about nine months ago, I had been in a long-term relationship. I had been with the same guy for about five years. It was a pretty good relationship, emotionally, but sexually…I don’t know. Big Mama probably told you this already, but I’ve never had an orgasm before.” He nodded as he took a drag of his cigarette. “With Brian, that was my boyfriend, we had sex often and it always did feel nice, but I could never climax. I’m ashamed to say that I ended up faking orgasms. He could never tell. Out of guilt, I finally admitted it to him after years of doing it and that’s what led to our break-up. Since then, I’ve been having all sorts of random sex, trying to figure out how to get myself to come. I haven’t had any luck, so I figured I’d see a “professional” before I saw a professional.”

                “No wonder she booked you with me,” he said with a smile. “I won’t promise you that I will manage to make you come, which is honestly something I never thought I’d say, but I will promise that I will try hardest and that we’ll have a lot of fun together. Sound good?”

                She nodded and finally gathered up the courage to lift up her head and look him in the eyes. Those brilliant blues smiled back at her and she could already feel herself moistening.

                “So how do you normally meet men, Rachel? It seems like you’re nervous about fucking a prostitute, so I’m thinking that we might do a little bit of roleplay to help make you more comfortable.”

                “I tend to hang out at bars and bring guys home from there,” she replied.

                “Perfect. I want you to go home and relax. Around 8ish, come to the bar at the corner of 7th and Main, and we’ll see how things go from there.” He took her chin in his fingers, angling her face up to his, and leaned down so that his lips were almost touching hers. “I’m really looking forward to getting to _know_ you.” She let out a shaky breath and leaned back, dropping his hand, and smiling. He never got tired of eliciting that reaction from people.

* * *

 

                Rachel sat at the bar nursing a glass of Pinot Grigio. She had been sitting alone for only about fifteen minutes, but it felt like so much longer. She tilted back her head and finished off her glass, feeling the warmth of the liquor flow through her body. She looked at herself in the mirror behind the bar. She hadn’t dressed too fancy, but she did use a curling iron to give her hair a few soft waves and she wore a little black dress that she honestly hadn’t worn in ages. She smiled at her reflection. Dammit, she did look pretty tonight.

                The bartender leaned down slightly to get into her field of view, bringing her back to reality. “A drink from the man at the end of the bar,” he said, smiling and nodding his head to the left as he placed a fresh glass of wine in front of her. She thanked him and then cautiously glanced to the side. Her face immediately burst into bright red.

                He slid up onto the stool next to her and leaned against the bar. “Well hello there,” he said smoothly. She began to giggle profusely. “What’s so funny, cutie?” he asked.

                She turned to look at him and she immediately stopped laughing. He was wearing a well fitted black suit, but his hair was disheveled like he just got out of the shower. It was a strange combination of looks, but it still managed to make her lose her breath for a moment.

                “It’s nothing. Were you the one who bought me a drink?” He nodded as he took a sip of his own glass of whiskey. “Thank you. That was very kind of you.”

                He set the glass down and wiped his bottom lip with his thumb. “You’re welcome. I’d give you some lame pick-up line, but I don’t think that’d work on you, right?”

                She laughed and slowly ran her fingers up and down the stem of the glass. I’d probably need about three more of these before a cheap line would work.”

                “Bartender! Three more Pinot Grigio’s, stat!”

Her shoulders hunched over as she laughed. She sat back up and wiped away a tear. “You are just too cute. I’m Rachel. Pleased to meet you.” She smiled genuinely and held out her hand. He took it in his and placed his other hand on top.

“You can call me Dean, sweetheart.”

* * *

 

                “Do you often let strange women take you back to their place?” she gasped out after they broke away from a long, breathy kiss.

                “Only when they laugh at my lame jokes and fit perfectly in my lap.” He squeezed her thighs and she let out a short yelp. She had been careful to not fully seat herself in his lap because she was afraid of what she might do in the cab if she were to feel his pelvis against hers.

                The car finally pulled up to the curb and they pulled themselves away from each other long enough to pay the driver and exit the car. Rachel collected herself and smoothed down her dress. She didn’t want to make a scene when she went up to her apartment. She stood in the lobby, calmly waiting for the elevator when Dean came up behind her and wrapped his arm around her waist. Her heart started beating fast again and her breaths became shorter.

                “How long is it going to take for this damn elevator to get here?!” she cried out.

                “You sure are eager. I like that.” He pinched her bottom and she quietly whimpered.

                “You are so not helping right now.”

                “I wasn’t trying to,” he chuckled.

                When the elevator finally arrived, they stepped in, and as soon as the door shut, Rachel jumped up onto him and proceeded to devour his neck. When they reached her floor, she quickly hopped down and cleared her throat.

                “I like to pretend that I’m a classy lady when I’m in public,” she said as she led him down the hall to her apartment.

                “And what are you in private?” he asked as he took off his sports coat.

                She unlocked door and stepped inside, grabbing his tie and pulling him in. “I like to think of myself as a playful rogue.” The door clicked shut behind them and she quickly began working her fingers over the buttons of his shirt. “I’d tear this right off of you right now if I didn’t think I’d be charged for damaging the goods.”

                He laughed as he loosened his tie and slipped it over his head. “I wouldn’t charge you for it, but I’d be stuck without a shirt.” They both stumbled forward toward her bedroom, kicking off their shoes in the process.

                She finally managed to open up his shirt, pressing her sweaty palms against his warm tight flesh. “I’m pretty sure no one would be complaining. I mean, have you looked at yourself lately?”

                He didn’t answer. He just picked her up, his hands cradling her ass, and carried her into her bedroom. He placed her down on her bed while they exchanged breaths, their tongues lightly touching one another so that they could just get a hint of what the other was drinking that night. He pulled away from her and started to remove his belt.

                “Take that damn dress off before I rip it off of you.” She laughed and he stopped and stared at her. “You think I’m joking, sweetheart? I have destroyed many dresses over the years. If you like yours, I’d get naked right now.”

                She bit her lip and swallowed hard. She had never been bossed around like that before. Most men had just done the usual sex run-down. A little bit of foreplay, then penetration, sprinkled with the typical stock dirty talk. There was something about Dean being a bit aggressive that made her feel more turned on then she ever had before.

                She watched him strip down completely, not moving an inch to follow his lead.

                “So you want to play this way? Is this what you like?” he asked.

                “I never knew before, but apparently. The threat of you getting aggressive is getting me going.”

                “Oh really, is it now?” He slowly walked up to her and leaned down, wrapping her hair around his fingers and lightly tugging back. “I’ll keep that in mind.” He lightly grazed his bottom teeth up her neck, eliciting a whimper from her.

Just as his mouth was about to reach her ear, he pulled away and let go. He grabbed a chair and fell back into it, crossing arms behind his head and propping his feet up on the bed. The sight of him fully stretched out like that was torture to her. “But why?!” she whined. “I hate begging, but I really want you to fuck me right now.”

“Patience, sweetheart, patience. I’m here to try to help you discover your orgasm, remember? I’m a man of my word, so let’s try something. Have you ever been able to come from masturbation?”

“No. I don’t really masturbate much because of that.” She looked honestly disappointed.

“Well, Rachel, I would like you to touch yourself for me. I want you to lift that skirt up, pull those panties down around your ankles and make yourself feel good.”

She complied quickly and gently touched between her legs with her fingers. She was much wetter than she thought she’d be. In all honestly, she was wetter than she had ever been with anyone else. She rubbed her two fingers between her slick lips, lightly teasing her clit as they passed by. After a moment, she stopped over her clit and began to rub slow circles around it. She sank deeper into the bed sheets as her body started to tingle with pleasure.

“That’s it. Keep that up.” He sat up and leaned forward, his arms resting on his thighs. “Do you know just how hot it is to watch a woman pleasure herself? It’s the most beautiful thing in the world. How does it feel?”

She took a few deep breaths before she answered. “It feels really good. But this is what I’m used to. A very nice plateau feeling, but never an actual orgasm.”

“Hmm.” He rubbed his chin with his hand as he thought. He stood up and moved over to her side. He knelt down and started to nibble at her neck, leaving more bites than kisses. He pushed her head to the side, exposing more of her neck and collarbone for him to devour. “How does this feel? Whenever I try something, I want you to tell me how it’s making you feel. Communication is going to be important here.”

She nodded with a look of slight pain on her face. “The biting feels good. I think my neck is very sensitive.”

He slowly ran the tip of his tongue from her collarbone up to her ear. He bit the tip of her earlobe and whispered, “I’m going to fuck you right now. That’s what you want, right?” She nodded quickly, her mouth pursed shut so that no stray moans escaped. “Now what I want you to do is continue rubbing that cute little clit of yours while I thrust, got that?” She nodded again.

He grabbed a condom from his sports coat, crawled up between her legs and lifted them so that they were resting against his hips. He rolled it onto his fully hard length and teasingly pressed the tip against her entrance, rubbing it in circles.

“Are you trying to fucking kill me here? Just shove it in, you jerk!”

He quickly brought his face down to hers, one of his hands lightly wrapped around her throat. “Do you want to say that again, but more politely this time?”

“No because I really like your hand around my throat like this,” she sighed.

“You dirty girl. You really are a bit of a rogue, aren’t you?

 He slowly pushed his cock between her wet folds, letting out a low grunt as he did. He started off slowly, eventually gaining speed and settling into a steady rhythm. Rachel quietly moaned his name when he squeezed her throat a little tighter. Her fingers were moving much faster now and he suspected that she may be close.

“How are you, babe? Can you come for me?”

“It feels good. Really good. But I don’t know if I’m close or not. I don’t know how to tell.” He could tell that she was beginning to get frustrated.

He let go of her throat and gripped tightly onto her thighs as he began to thrust much faster and harder. He thought perhaps something a bit rougher and deeper might help her get over this plateau.

The minutes continued on, but the results were still the same.

“I give up! This just isn’t working! There’s something wrong with me and I don’t want to waste your time anymore.” She covered her face with her hands and let out a muffled yell.

“I’m not giving up on you yet. We can do this.”

“How are you so sure?”

“Because I’m Dean fucking Ambrose, and I’m damn good at my job. Now do you trust me?” She sighed and said yes. “Okay, you are clearly in your head about this. I want you to just relax. Don’t think about the orgasm. Don’t think about anything. Just let yourself go. Get on your knees and turn around.”

He held her tightly against his chest and eased her back onto his cock. He guided her hand back to her clit and began to slowly thrust up into her. He pulled her body up and down in time with his thrusts, making sure to go as deep as he could. He used one hand to cup her breast, softly running his fingers along her hardening nipple. He buried his face in her hair and listened to her soft moans. For two strangers in a very strange situation, it was quite romantic.

Eventually her moans became louder. His instinct told him to thrust faster and harder, but he held himself back and continued the slow, deep grinding motion. He started to bite at her neck when he felt her body tightening. He knew the familiar signs. He had seen them hundreds of times before. He kissed her ear and moaned, “Let yourself go, Rachel. I want to feel your pussy tremble.”

Her orgasm was oddly silent. She held her breath as it swept over her. He knew by her facial expression and how her walls tightly gripped onto his cock, though, that it was a deep full body orgasm. He held her there for a moment while she let the feeling slowly fade away and her heart beat return to normal. Her eyes slowly fluttered open and they looked glossy with tears.

“Are you getting emotional on me?”

She sniffed and wiped away a tear with the back of her hand. “Sue me. I’ve been waiting to feel this for years and now I know that I don’t have a medical or psychological problem. I’m a bit emotional right now.”

He smiled and kissed her temple. “Congratulations.” She laughed and pulled herself off of him. She then turned around and reached out to give him a tight hug. She leaned back and a sheepish grin appeared on her face.

“What?” he asked.

“Umm…would it be possible for me to have another one of those?”

He laughed smugly. “Sweetheart, I can go all fucking night.” 

* * *

 

The next morning as Dean groggily stumbled back into the house, an early morning cigarette hanging between his lips, I peeked out from my office door and smiled at his disheveled look.

“Long night, my love?”

“Challenge accomplished, Mama,” he said with that cocky grin that I adored.

“I knew you could do it. I’m guessing that you both really enjoyed yourselves, hmm?”

“Yeah. It was actually a lot more fun than I thought it would be. How do you know, though? Is it my hair? Cause my fucking hair is always like this.”

“Yes, that is part of it,” I said with a wide wicked grin. “But also because she’s already booked you for three more visits.”


	3. Ambrose and the Frustrated Spanko

Mondays are designated days off for my boys. Some of them are constantly booked up, so this makes sure that they have a day to rest. You know how tiring it can be to always be trying to make people happy. On Monday nights, I bring them to my favorite bar. Mondays are not a popular drinking night, generally, so the bartenders appreciate the extra business. In all honesty, we're usually the only ones there, except for a few regulars who always sit on the end of the bar closest to the door and never bother us.

I do it to make my boys happy and let them hang out together, but I also do it because I enjoy watching them with a little alcohol under their belt. Most of them are not bound by many inhibitions as it is, but they do get awfully giggly when tipsy and I find that remarkably cute.

So as this Monday night progressed, I had settled into my spot at the bar with my glass of brandy and was admiring my boys when I noticed the bartender on duty staring at them as well. Now don't get me wrong. I wasn't upset at her for looking at them. That would be absurd. I want everyone to look at my boys because everyone is a prospective client. No, what I found odd was that she had never really seemed to take notice of them before in all the times that we had been here.

She was a sweet girl. Annabel was her name. She had lovely raven colored hair and she looked mature for her age, a detail that was usually accompanied by an almost permanent scowl on her face.

"What's troubling you, sweetheart?" I asked.

She almost seemed startled that I was even speaking to her. I think she had gone into a bit of a trance while looking at my ridiculous boys laughing and throwing napkins at each other like a bunch of drunk children.

"Oh, sorry Mama. Did you want another brandy?"

"No, dear. I'm still nursing this one. I just noticed that you were staring at my boys," I laughed.

"Oh no! I'm sorry. That's not a very professional thing to do, is it?" She scratched the back of her head as she looked at me sheepishly.

"Bel, the staring was fine, you don't need to be ashamed. It's just that we're in here every week and you've never stared at them like that before. It was like you were in a trance and your mind was elsewhere, so I was wondering if something was troubling you."

"Ahh, it's just dumb guy stuff."

"What do you mean?"

"Well I've just never seemed to have much luck with men. I'll meet a guy I really like, but they just want to get in my pants. That wouldn't be so bad if they were upfront about it so I knew that it was just a sex fling, but even then, the guys never seem to be into what I'm into."

"And what would that be?"

"Spanking."

"Guys don't want to spank you?"

"Come on, Mama. You're in the business of sex, so you know what I mean. They don't ever seem to understand just how much I need to be spanked. It's like an instinctual inner desire for me or something. I just need to be disciplined. I can't quite explain it. Then, if the guy is willing to try, he just sort of taps my bottom and thinks that's a proper spanking. They're afraid to hurt me, but that's part of the whole experience."

"Hmm, I see what you mean."

"So I've casually dated a few guys and had one or two quick flings, but nothing has felt right. No one has been able to satiate this...thirst that I have. It's just really frustrating. Maybe I was subconsciously staring at the guys because I'm still pining for a proper spanking and they're there in front of me, being all handsome."

I laughed at her and she frowned.

"Sweetheart, it's entirely understandable to be sexually frustrated. A good chunk of my business comes from people with that issue. If you ever want to get rid of that frustration..."

"Oh geez. Mama, I don't think I could ever pay for sex. I can't afford it, for one thing, and I think I would hate myself. Like I would feel that I'm a failure for having to resort to that."

"You wouldn't be a failure, Bel. No one's a failure for not being able to find the person who best compliments them. Or for not being able to find a person who just 'gets them' sexually. It can be a challenge." I took one of my business cards from my purse and slid it toward her. "You can trust me, sugar. Whenever you feel ready, just give me a call."

"I don't think I'd ever be ready," she replied, although she picked up the card anyway and slipped it into the pocket of her jeans.

She went back to wiping down the bar and I returned to admiring my boys. I noticed that Jon had been watching me speak with Annabel. We made eye contact and then he glanced at her, then back at me. He raised his eyebrow and I nodded. I held up my hand, flat and with the fingers together, and flicked my wrist. He nodded back and smiled. This was why he was my favorite. We understood each other without saying a word.

Tonight, Annabel was going to get the release that she so craved.

* * *

I rounded up the boys and began to guide then outside. They were all drunk enough where they needed a little guidance, but not to the point of being obnoxious or a public nuisance. If any of them ever got that drunk, they got a rather aggressive talking to. You might laugh at the thought of me scolding these grown men like they were schoolboys, but trust me when I say that I can get pretty vicious when need be.

As I lured them out of the bar, Jon held back and strolled over to the bar where Annabel was getting ready to close up. He winked at me and I winked back as I let the door shut behind me.

He leaned against the bar, casually, yet with that aura of charisma that naturally drew people to him. He watched her for a moment, admiring her more superficial traits and smiling to himself. When she turned around, she jumped.

"I thought everyone had left!"

"They did," he shrugged. "I just decided to stick around for a while. If that's okay with you, of course." His mouth curled into the sort of grin that makes panties drop. It wasn't lost on Annabel.

She cleared her throat to try to somehow hide her flushed face. "No, uh, I don't mind. Any particular reason that you'd want to stay after closing? Do you want another beer?"

Dean shook his head. "Nope." He rested his head in his hand as he leaned against the bar and stared at her mischievously.

She shifted uncomfortably under his gaze. "Okay then…so…what do you want?"

"Nothing in particular. I've been keeping an eye on you all night."

"...really? Why?"

"Mmhmm...you just seemed a bit out of it today. You doing alright?"

"You're not going to charge me for this, are you?"

"Just to talk? Generally when someone is paying me, we're not talking," he said with a wink and a smile.

She frowned at him and looked away, her cheeks slowly becoming a light shade of rose.

"No, Bel. I'm not going to charge you. Don't be ridiculous. You're always so good to us, so this is me as a friend right now."

She sighed, accepting that he wasn't going to go away until she opened up to him. "I've been having a bit of guy trouble lately."

"Did some dude break up with you?"

"Not to go into specifics, but more or less. I just feel used and disappointed. I had opened myself up to him when I told myself I wouldn't and he took advantage of it. So that's been bugging me the last few days."

"I see. You should get back out there. Find someone to distract you for a little while, if you catch my drift."

"Dean, your drift is so obvious, I can see it from a mile away," she giggled, smiling for the first time that night.

"You should smile more. You're beautiful when you do."

By now Annabel's face was close to a shade of crimson. "Thank you, Dean." She shook her head and leaned against the bar. "I don't think that would help very much, going to find someone as a distraction. The kind of thing I'm looking for...it just doesn't seem like it's easy to find guys around my age who are into it. Every time I've tried dating sites online, I can only find older gents and I'm generally not very attracted to older men."

"What is it that you're looking for?" he asked, knowing full well what the answer was going to be.

"I need to be spanked."

"Well no one can ever say that you're not upfront about it," he said as he pushed the hair out of his eyes.

"I mean, if I was looking for someone to spend my life with, I'd include other criteria, but I'm only 22 and I just want to have some fun and spend time with someone casually. He doesn't need to be perfect..." she said, her voice drifting off. "He just needs to not stand me up and not spank me like a pussy," she mumbled under her breath.

"How do you want a guy to spank you, then?"

Annabel covered her mouth with her hand. "Fuck, you heard that?"

He laughed at her and placed his hand on his chest. "Hey man, you're talking to a fellow mumbler. I speak the language."

She shifted her weight back and forth on the balls of her feet. "I want it really hard. I want it to hurt. But I also want the guy to know what he's doing. Like, there's a method, a technique to a proper spanking that these guys don't seem to understand. It's just...frustrating. It's never as sexually fulfilling as I wish it was. As I feel it should be."

"I see," he said, rubbing his chin.

"And to top off my downer mood lately, I feel like my professional life is in shambles. I have a degree and what do I have to show for it? I tend bar at this place. I wish I had a better job, but it's been so hard trying to find one around here."

"I'm glad you work here because I get to see you every week." His smile was enough to charm her into believing him.

"You're probably just saying that to make me feel better, but I'll take it."

"So your personal and professional lives are both feeling pretty shitty lately?"

"Extremely shitty, and the prospect of that changing doesn't look great."

"It sounds like you need a little structure...a little discipline in your life." He waved her over to him with his hand. "Come over here." He pulled out one of the wooden chairs and sat down facing her. She hadn't moved an inch. He shot her a disapproving look. "I mean it, Annabel, get over her now."

The hard look on his face and the sternness in his voice made her legs shake as she slowly came around the bar and walked forward. She stopped in front of him. Her hands fidgeted in front of her and she looked at the ground. She couldn't quite get herself to look him in the eyes right now.

"Annabel. Look at me."

She lifted her eyes, peeking at him through her lashes, but she didn't lift her head. She felt so embarrassed. He grabbed her chin firmly and pushed it up so that they were face to face. Her cheeks were turning from a pleasant pink to a bright red.

"I want you to lie down over my lap."

"Seriously?" she asked.

"Do I look like I'm joking?" His eyes were rigid and intense.

Gulping, Annabel shook her head. She slowly lowered herself across his thighs, but it was apparently too slow for Dean.

"Get down there," he said as he pushed down on her back and pulled her into the proper position. "This is what you want, right? That's what you said."

"Yes," she nodded. "Yes, please."

"Now tell me. Why do you deserve to be spanked?" he asked as he started to rub his hand along her jean-covered bottom.

"I can't quite seem to get my life together."

"I should smack your ass for being too general. Give me something specific to punish you for...or I'll punish you for failing to follow the rules."

"My life is unorganized. I need some structure. Some rules. Some guidance to make myself better and progress as an adult."

"That's a very mature answer. Good girl." He squeezed her ass playfully and she let out a squeak of surprise. "I might not be able to keep you in check all of the time, but I think I can help you get started."

He pressed his left hand down firmly onto her back and lifted his right hand. Annabel inhaled sharply, knowing what was about to happen. Dean brought his hand down hard onto her right cheek, then repeated the same action on the left one.

Annabel winced, but did not cry out. This wasn't her first rodeo, so she knew what to expect. She would have to admit, however, that his hands were larger and stronger than any of the guys she had been intimate with previously.

"Those were just two warning shots. Do you still want to go through with this?"

She took a deep breath and nodded. "Please god, yes."

He made a low noise that softly rumbled in his throat. Annabel wasn't quite sure what it was. A moan? A growl? Whatever it was, though, she knew she wanted to hear it again.

He gave her ass another gentle rub and then without much of a pause, he began to smack her bottom hard and at a steady, upbeat pace. Thwack. Thwack. Her body lurched forward a tiny bit every time his heavy hand made contact. Thwack. Thwack. Behind the pain, there was a deliciousness about it that she would never be able to put into words to try to explain to others. It was just something she felt deep inside. Her breath became heavy and right before he let up, she was about to crack and cry out.

"Get up and take your pants off," he ordered.

She awkwardly tried to pick herself up off of his lap, but he wouldn't help her. Once she was finally standing again, she noticed that he had been watching her very closely. She started to unfasten the button on her jeans, but her fingers couldn't quite get it with him staring at her. They had talked so easily and casually just moments before, yet now there was this different aura about him. He was really taking this dominant role to heart.

"Faster. Quit stalling, Annabel. You need to take your spanking like a good girl."

He was flexing the fingers of his right hand like he was warming them up. The sight of that alone made her feel a little dizzy and her pussy began to ache. She could still feel her bottom throbbing slightly. She bit her lip, anticipating what was to come next. She managed to finally remove her pants and she went to stand next to Dean.

"Very nice," he smiled when he saw the panties she was wearing that night. He pointed to his lap and his smile turned stern. "Get down here, now."

She obeyed him immediately and he praised her for it. His hand returned to her ass, gliding along the thin fabric of her panties.

"This feels so nice," he said. "You over my knees. My hand teaching you a lesson." He began to spank her again as he said the word "lesson".

Without the thick covering of her jeans, Annabel could feel the sting of his hand much more. She didn't want to make any noise, but she just couldn't help it after the first few smacks. It started off as a soft whimper, barely audible. It soon grew into a muffled whine. She was clearly feeling the rawness in her skin, but she kept her lips tightly pressed together. She didn't like crying during a spanking, and she refused to do so now.

"It's okay, you can cry. I know it hurts." She shook her head defiantly. He paused for a moment to turn her head up towards him and he leaned down and looked in her eyes. "I want you to cry, Annabel. That's the only way I'll know that this is working. This is how the message will get through." She shook her head again.

"Fine, if you want it that way…" He let go of her face and brought both hands to her hips. Grabbing the top of her panties, he forced them down until they were sitting around the middle of her thighs. Her flesh was already a pleasant baby pink color, but he wanted to see red. "I will make you cry."

He pushed down firmly on the middle of her back and began to unleash a flurry of heavy slaps to her bare ass. Annabel had never had such a hard spanking before. She had always wished that a guy would go as hard as Dean was at that moment, but now that she was getting her wish, she wasn't really sure if it was what she wanted. Right now, everything just felt like it was too intense. It was too much.

It took her a few seconds to realize that she was crying. It wasn't a hysterical sobbing sort of cry, but it was immensely cathartic and exactly what she needed right now. She watched as her tears dripped off of her face and hit the wooden floor below her. A few wails managed to escape from her mouth and she heard him whisper, "That's my girl."

After a few more smacks, Dean let up, taking his right hand and lightly placing it on her lower back. He rubbed his hands gently along her back, trying his best to help her come down from this experience. He leaned down and wrapped his arms around her as best he could. It was an awkward sort of position, but he didn't want to sit her on his knee right now, as her bottom was hypersensitive.

"You did very well, Bel. I'm very proud of you." He lifted her head up and kissed the top of it. Despite some tears still welled in her eyes, she smiled.

"Thank you for that," she whispered.

"It was my pleasure."

He glided a hand up her inner thigh until he reached her bare pussy. Her outer lips were already slick with wetness. He could only imagine how wet she must be inside.

"Damn, you weren't lying when you said you craved a spanking." He traced a finger between her lips, eliciting a soft moan from her throat. He parted her legs slightly so he could have easier access to her entrance. He slid two fingers in with ease as she wriggled on his lap.

"You are so wet and open right now." He felt himself quickly harden underneath her. He had been a little hard during the spanking, but seeing just how aroused she was right now was a huge turn on.

He picked her up off of his lap and helped her onto her feet. He stood up and pressed his lips against hers while he fumbled with his pants.

She broke away from the kiss with a gasp. "I so badly want to fuck you, but I told you I can't afford it."

"That spanking was me helping out a friend," he panted. "This right here is me about to fuck you because I want to. Now take your shirt off and let me see those tits."

She wasn't about to let embarrassment stop her from giving him what he asked for. She pulled her top up and over her head, tossing it over to where her jeans had landed earlier. She also decided it was time to fully take off her panties, which quickly joined the rest of her clothes.

He had finally managed to unhook the button of his pants and pull down the zipper. He was attempting to pull out his cock when Annabel grabbed the waist of his pants and pulled then down to his ankles.

"If I'm getting to have this moment, I'm going to get the whole view."

He laughed at her sudden boldness as he kicked his pants behind him. "I suppose my shirt has to go too then, yeah?"

She nodded and crouched down in front of him to work on removing his boxers. When his cock sprung out from behind the fabric, she leaned back and took in the view.

"You like what you see?" He laughed.

"It's even better than I imagined. Ever since you guys started coming here once a week, I've honestly always wondered what it would be like to fuck you. I…sometimes stare at you when you're not looking." Her whole body had been flushed for a while, but he could still tell that she was blushing from admitting that.

"I've actually thought about what it'd be like to bang you, too. Sometimes you absentmindedly suck on cherries when it's slow in the bar, and goddamn woman, it looks like you could do some amazing things with that mouth of yours."

"I flattered, but if you want to try that out, it'll have to be another time because I need your dick in my pussy right now."

"Yes, ma'am," he laughed.

He quickly grabbed a condom from his pants and returned to her as he rolled it on with ease.

"You're quite good at that," she said.

"I hope I'd be with how often I put them on," he chuckled. He sat back down in the chair and crooked his finger at her. "Now get that fine ass of yours over here so I can look at my handiwork."

He reached his hand out to her and she took it, stumbling a bit as his tugged her toward him. He turned her around and traced his finger along the red raised welts that were in the vague shape of his hand. She shuddered at the slight touch. Her nerves were still on high alert and her skin was tender and sore.

He spread his legs slightly, placed his hands on her hips and pulled her down like she was going to sit in his lap. He held her around her waist for a moment while he lined up his cock to her waiting hole, then he let her weight sink herself down around him.

His dick felt amazing, filling her completely. She could feel him throbbing, even through the condom. She let out a long moan as her circled his hips while he was balls deep within her. He held her low around her waist and she feared for a moment that her weight would give and she would fall, hurting herself and seriously hurting Dean. After a moment, though, she felt confident that she was safe in his strong arms and let herself go.

He rocked her back and forth so that her hips slid up and down his cock. Slow and deep, it felt great, but it was also like a great tease to Annabel, who was used to being fucked fast and furious. She covered her breasts with her hands and began to massage them at the same speed that their bodies were rocking together.

He looked down over her shoulder and watched her with a smirk on his face. "One of my favorite things in the world is watching a woman pleasure herself," he whispered in her ear. She let her head roll back against his shoulder so he could have a better look.

After a while, he straightened her up and stood up himself. He gently pushed her so that she started walking toward the bar. She got the hint, bent over slightly, and leaned against the bar. He dug his fingers into her hips and slid back inside of her, thrusting at a furious pace. He cupped a hand on one of her breasts and the other hand slipped between her legs. His pelvis slapped against her ass with each thrust, sending shivers of pain and pleasure through Annabel's body.

She felt the tension building between her legs as he rubbed his fingertips against her clit and roughly pinched her nipple between his fingers. She finally released around his cock when he bit down on her earlobe. The cries of her orgasm sounded vaguely similar to the cries she made during the spanking.

"Mmm," he moaned. "You sound fucking wonderful when you come."

He gave a few more thrusts before his body went rigid and he thrust in deep, spilling his cum into the condom. They stood there for a few minutes, his arms still wrapped around her, as they came down from their high.

Once they had cleaned up a bit in the bathroom and got dressed again, a painful reality hit Annabel in the face.

"Fuck. I still haven't cleaned the bar yet." She hit her head with the palm of her hand and then went to grab the cleaning supplies.

"Let me help you so you can get out of here," he offered.

"That would be wonderful."

With the two of them working together, it only took about a half an hour to clean up the small bar. The two of them stood outside as she locked up.

"Hey," he mentioned. "Would you like me to walk you home? It's late and I wouldn't feel right leaving you alone, especially after we fucked and everything."

"You make it sound so romantic. Yes, thank you. I would really appreciate that."

"Alright then, let's go." He gave her a smack on her ass as he strutted past her. She glared at him with a big smile on her face and rubbed her sore butt as they headed into the night.


End file.
